Organic electroluminescence device and monoamine compound for organic electroluminescence device

ABSTRACT

An organic electroluminescence device of an embodiment includes a first electrode, a second electrode on the first electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer includes a monoamine compound including a condensed three ring hetero compound and a condensed four ring hetero compound as substituents, and wherein the condensed four ring hetero compound includes two of at least one atom of an oxygen atom or a sulfur atom.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation of U.S. application Ser. No.16/745,137, filed Jan. 16, 2020, which claims priority to and thebenefit of Korean Patent Application No. 10-2019-0032405, filed on Mar.21, 2019, the entire content of which is hereby incorporated byreference.

BACKGROUND

Embodiments of the present disclosure herein relate to an organicelectroluminescence device and a monoamine compound for an organicelectroluminescence device.

Recently, the development of an organic electroluminescence device as animage display device is being actively conducted. Different from aliquid crystal display device, the organic electroluminescence device isa self-luminescent display device in which holes and electrons injectedfrom a first electrode and a second electrode recombine in an emissionlayer, and a light emission material including an organic compound inthe emission layer emits light to attain display.

In the application of an organic electroluminescence device to a displaydevice, the decrease of the driving voltage, and the increase of theemission efficiency and the life of the organic electroluminescencedevice are beneficial, and development on materials for an organicelectroluminescence device which is capable of stably attaining therequirements is being continuously researched.

SUMMARY

Embodiments of the present disclosure provide an organicelectroluminescence device and a monoamine compound for an organicelectroluminescence device, and, for example, an organicelectroluminescence device having high efficiency and a monoaminecompound included in a hole transport region of the organicelectroluminescence device.

An embodiment of the present disclosure provides an organicelectroluminescence device including a first electrode, a secondelectrode on the first electrode, and an organic layer between the firstelectrode and the second electrode.

The organic layer includes a monoamine compound including a condensedthree ring hetero compound and a condensed four ring hetero compound assubstituents. The condensed four ring hetero compound includes two of atleast one atom of an oxygen atom or a sulfur atom.

In an embodiment, the condensed three ring hetero compound may includeany one selected from a nitrogen atom, a sulfur atom and an oxygen atom.

In an embodiment, the hetero compounds may be each independentlycombined with an amine group via a linker or a direct linkage.

In an embodiment, the organic layer may include a hole transport regionon the first electrode, an emission layer on the hole transport region,and an electron transport region on the emission layer. The holetransport region may include the monoamine compound.

In an embodiment, the hole transport region may include a hole injectionlayer on the first electrode, and a hole transport layer on the holeinjection layer. The hole injection layer or the hole transport layermay include the monoamine compound.

In an embodiment, the monoamine compound may be represented by thefollowing Formula 1:

In Formula 1, X is NAr₂, S, or O, A and B are each independently O or S,Ar₁ and Ar₂ are each independently a substituted or unsubstituted arylgroup of 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroaryl group of 2 to 30 carbon atoms for forming aring, R₁ to R₄ are each independently a hydrogen atom, a deuterium atom,a halogen atom, a cyano group, a substituted or unsubstituted alkylgroup of 1 to 20 carbon atoms, a substituted or unsubstituted aryl groupof 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroaryl group of 2 to 30 carbon atoms for forming aring, L₁ and L₂ are direct linkages, substituted or unsubstitutedarylene groups of 6 to 30 carbon atoms for forming a ring, orsubstituted or unsubstituted heteroarylene groups of 2 to 30 carbonatoms for forming a ring, “a” and “b” are integers of 0 to 4, “c” and“d” are integers of 0 to 3, and “m” and “n” are integers of 0 to 2.

In an embodiment, Formula 1 may be represented by the following Formula2 or Formula 3:

In Formula 2 and Formula 3, X, Ar₁, R₁ to R₄, L₁, L₂, “a” to “d”, “m”and “n” are the same as defined with respect to Formula 1.

In an embodiment, Formula 1 may be represented by the following Formula4 or Formula 5:

In Formula 4 and Formula 5, X, Ar₁, R₁ to R₄, L₁, L₂, “a” to “d”, “m”and “n” are the same as defined with respect to Formula 1.

In an embodiment, “m” and “n” may be each independently 0 or 1, and L₁and L₂ may be each independently a direct linkage or a substituted orunsubstituted arylene group of 6 to 12 carbon atoms for forming a ring.

In an embodiment, Ar₁ may be a substituted or unsubstituted aryl groupof 6 to 18 carbon atoms for forming a ring.

In an embodiment, Formula 1 may be represented by the following Formula6:

In Formula 6, X, A, B, Ar₁, R₁ to R₄, L₁, L₂, “a” to “d”, “m” and “n”are the same as defined with respect to Formula 1.

In an embodiment of the present disclosure, there is provided an organicelectroluminescence device including a first electrode, a secondelectrode on the first electrode, and an organic layer between the firstelectrode and the second electrode. The organic layer includes themonoamine compound represented by Formula 1.

In an embodiment, the organic layer may include a hole transport regionon the first electrode, an emission layer on the hole transport region,and an electron transport region on the emission layer. The holetransport region may include the monoamine compound represented byFormula 1.

BRIEF DESCRIPTION OF THE FIGURES

The accompanying drawings are included to provide a furtherunderstanding of the subject matter of the present disclosure, and areincorporated in and constitute a part of this specification. Thedrawings illustrate exemplary embodiments of the present disclosure and,together with the description, serve to explain principles of thepresent disclosure. In the drawings:

FIG. 1 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the presentdisclosure;

FIG. 2 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the presentdisclosure;

FIG. 3 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the presentdisclosure; and

FIG. 4 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the presentdisclosure.

DETAILED DESCRIPTION

Features of embodiments of the present disclosure will be easilyunderstood from the description herein of embodiments of the presentdisclosure with reference to the accompanying drawings. The subjectmatter of the present disclosure may, however, be embodied in differentforms and should not be construed as limited to the embodiments setforth herein. Rather, exemplary embodiments are provided so that thedisclosure herein will be thorough and complete, and the spirit andscope of the present disclosure is sufficiently clear for a personskilled in the art.

Like reference numerals refer to like elements throughout. In thedrawings, the dimensions of structures may be exaggerated for clarity ofillustration. It will be understood that, although the terms first,second, etc. may be used herein to describe various elements, theseelements should not be limited by these terms. These terms are only usedto distinguish one element from another element. Thus, a first elementcould be termed a second element without departing from the spirit andscope of the present disclosure. Similarly, a second element could betermed a first element. As used herein, the singular forms are intendedto include the plural forms as well, unless the context clearlyindicates otherwise.

It will be further understood that the terms “comprises” and/or“comprising,” when used in this specification, specify the presence ofstated features, numerals, steps, operations, elements, parts, or thecombination thereof, but do not preclude the presence or addition of oneor more other features, numerals, steps, operations, elements, parts, orthe combination thereof. It will also be understood that when a layer, afilm, a region, a plate, etc. is referred to as being “on” another part,it can be directly on the other part, or intervening layers may also bepresent. In addition, when a layer, a film, a region, a plate, etc. isreferred to as being “under” another part, it can be “directly under”the other part, or intervening layers may also be present. Additionally,it will also be understood that when an element or layer is referred toas being “between” two elements or layers, it can be the only element orlayer between the two elements or layers, or one or more interveningelements or layers may also be present.

First, an organic electroluminescence device according to an embodimentof the present disclosure will be explained with reference to FIGS. 1 to4 .

FIG. 1 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment. FIG. 2 is across-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment. FIG. 3 is across-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment. FIG. 4 is across-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment of the presentdisclosure.

Referring to FIG. 1 , an organic electroluminescence device 10 accordingto an embodiment of the present disclosure includes a first electrodeEL1, an organic layer OL and a second electrode EL2. The first electrodeEL1 and the second electrode EL2 face each other, and the organic layermay be between the first electrode EL1 and the second electrode EL2.

When compared with FIG. 1 , FIG. 2 shows the cross-sectional view of anorganic electroluminescence device 10 of an embodiment, wherein theorganic layer OL includes a hole transport region HTR, an emission layerEML, and an electron transport region ETR.

In addition, when compared with FIG. 2 , FIG. 3 shows thecross-sectional view of an organic electroluminescence device 10 of anembodiment, wherein the hole transport region HTR includes a holeinjection layer HIL and a hole transport layer HTL, and the electrontransport region ETR includes an electron injection layer EIL and anelectron transport layer ETL.

In addition, when compared with FIG. 2 , FIG. 4 shows thecross-sectional view of an organic electroluminescence device 10 of anembodiment, wherein the hole transport region HTR includes a holeinjection layer HIL, a hole transport layer HTL, and an electronblocking layer EBL, and the electron transport region ETR includes ahole blocking layer HBL, an electron transport layer ETL and an electroninjection layer EIL.

The organic layer OL includes the monoamine compound according to anembodiment of the present disclosure. Hereinafter, the monoaminecompound according to an embodiment of the present disclosure will beexplained in more detail, and each layer of the organicelectroluminescence device 10 will be explained.

As used in the present description, the term “substituted orunsubstituted” corresponds to substituted or unsubstituted with at leastone substituent selected from the group consisting of a deuterium atom,a halogen atom, a cyano group, a nitro group, a silyl group, a borongroup, a phosphine group, an alkyl group, an alkenyl group, an arylgroup, and a heterocyclic group. In addition, each of the substituentsmay be substituted or unsubstituted. For example, a biphenyl group maybe interpreted as an aryl group or a phenyl group substituted with aphenyl group.

In the present description, examples of the halogen atom may include afluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the present description, the alkyl group may be a linear, branched,or cyclic type (e.g., a linear, branched, or cyclic alkyl group). Thenumber of carbon atoms of the alkyl group may be 1 to 30, 1 to 20, 1 to10, or 1 to 4. Examples of the alkyl group may include methyl, ethyl,n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl,3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl,1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl,n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl,4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl,2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl,2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl,n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl,2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl,2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl,n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl,2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl,2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl,n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl,n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.,without limitation.

As used in the present description, the term “aryl group” refers to anoptional functional group or substituent derived from an aromatichydrocarbon ring. The aryl group may be a monocyclic aryl group or apolycyclic aryl group. The number of carbon atoms for forming a ring inthe aryl group may be 6 to 30, 6 to 20, or 6 to 12. Examples of the arylgroup may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl,biphenyl, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl,biphenylene, triphenylenyl, pyrenyl, benzofluoranthenyl, chrysenyl,etc., without limitation.

In the present description, the fluorenyl group may be substituted, andtwo substituents may be combined with each other to form a spirostructure. Examples of the substituted fluorenyl group may include thefollowing. However, embodiments of the present disclosure are notlimited thereto.

In the present description, the heteroaryl group may include one or moreselected from O, N, P, Si and S as a heteroatom. In an embodiment, wherethe heteroaryl group includes two heteroatoms, the two heteroatoms maybe the same or different. The number of carbon atoms for forming a ringof the heteroaryl group may be 2 to 30, or 5 to 12. The heteroaryl groupmay be monocyclic heteroaryl group or polycyclic heteroaryl group. Thepolycyclic heteroaryl group may have, for example, a two-ring orthree-ring structure. Examples of the heteroaryl group may includethiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole,triazole, pyridine, bipyridine, pyrimidine, triazine, triazole, acridyl,pyridazine, pyrazinyl, quinoline, quinazoline, quinoxaline, phenoxazine,phthalazine, pyrido pyrimidine, pyrido pyrazine, pyrazino pyrazine,isoquinoline, indole, carbazole, N-arylcarbazole, N-heteroarylcarbazole,N-alkylcarbazole, benzoxazole, benzoimidazole, benzothiazole,benzocarbazole, benzothiophene, dibenzothiophene, thienothiophene,benzofuran, phenanthroline, thiazole, isooxazole, oxadiazole,thiadiazole, phenothiazine, dibenzosilole, dibenzofuranyl, etc., withoutlimitation.

In the present description, the silyl group may include an alkyl silylgroup and an aryl silyl group. Examples of the silyl group may includetrimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl,propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.However, embodiments of the present disclosure are not limited thereto.

In the present description, the explanation of the aryl group may alsobe applied to the arylene group except that the arylene group is adivalent group.

In the present description, the explanation on the heteroaryl group mayalso be applied to the heteroarylene group except that the heteroarylenegroup is a divalent group.

In an embodiment, the monoamine compound includes a condensed three ringhetero compound and a condensed four ring hetero compound assubstituents, and the condensed four ring hetero compound includes twoselected from at least one atom of an oxygen atom or a sulfur atom. Forexample, the condensed four ring hetero compound which is included inthe monoamine compound may include two oxygen atoms. In someembodiments, the condensed four ring hetero compound which is includedin the monoamine compound may include two sulfur atoms. In someembodiments, the condensed four ring hetero compound which is includedin the monoamine compound may include one oxygen atom and one sulfuratom.

The condensed three ring hetero compound included in the monoaminecompound may include at least one of a nitrogen atom, a sulfur atom oran oxygen atom.

In an embodiment, the condensed three ring hetero compound included inthe monoamine compound may be combined with an amine group via a linkeror may make a direct linkage with the amine group.

In an embodiment, the condensed four ring hetero compound included inthe monoamine compound may be combined with an amine group via a linkeror may make a direct linkage with the amine group.

The monoamine compound according to an embodiment is represented by thefollowing Formula 1:

In Formula 1, X is NAr₂, S, or O.

In Formula 1, A and B are each independently O or S.

In Formula 1, Ar₁ and Ar₂ are each independently a substituted orunsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, ora substituted or unsubstituted heteroaryl group of 2 to 30 carbon atomsfor forming a ring.

In Formula 1, R₁ to R₄ are each independently a hydrogen atom, adeuterium atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group of 1 to 20 carbon atoms, a substituted orunsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, ora substituted or unsubstituted heteroaryl group of 2 to 30 carbon atomsfor forming a ring.

In Formula 1, L₁ and L₂ are direct linkages, substituted orunsubstituted arylene groups of 6 to 30 carbon atoms for forming a ring,or substituted or unsubstituted heteroarylene groups of 2 to 30 carbonatoms for forming a ring.

In Formula 1, “a” and “b” are integers of 0 to 4. In some embodiments,if “a” is 2 or more, a plurality of R₁ groups are the same or different,and if “b” is 2 or more, a plurality of R₂ groups are the same ordifferent.

In Formula 1, “c” and “d” are integers of 0 to 3. In some embodiments,if “c” is 2 or more, a plurality of R₃ groups are the same or different,and if “d” is 2 or more, a plurality of R₄ groups are the same ordifferent.

In Formula 1, “m” and “n” are integers of 0 to 2. In some embodiments,if “m” is 2 or more, a plurality of L₁ groups are the same or different,and if “n” is 2 or more, a plurality of L₂ groups are the same ordifferent.

In an embodiment, “m” and “n” in Formula 1 may be each independently 0,and L₁ and L₂ may be each independently a direct linkage.

In an embodiment, “m” and “n” in Formula 1 may be each independently 1,and L₁ and L₂ may be each independently a substituted or unsubstitutedarylene group of 6 to 12 carbon atoms for forming a ring. L₁ and L₂, forexample, may be each independently a substituted or unsubstitutedphenylene group or a substituted or unsubstituted biphenylene group.However, embodiments of the present disclosure are not limited thereto.

In an embodiment, Ar₁ of Formula 1 may be a substituted or unsubstitutedaryl group of 6 to 20 carbon atoms for forming a ring. For example, Ar₁may be a substituted or unsubstituted phenyl group, a substituted orunsubstituted biphenyl group, a substituted or unsubstituted naphthylgroup, or a substituted or unsubstituted fluorenyl group. However,embodiments of the present disclosure are not limited thereto.

In an embodiment, A and B in Formula 1 may be the same atom. In someembodiments, Formula 1 may be represented by the following Formula 2 orFormula 3:

In Formula 2 and Formula 3, X, Ar₁, R₁ to R₄, L₁, L₂, “a” to “d”, “m”and “n” are the same as defined with respect to Formula 1.

In an embodiment, A and B in Formula 1 may be different atoms from eachother. In some embodiments, Formula 1 may be represented by thefollowing Formula 4 or Formula 5:

In Formula 4 and Formula 5, X, Ar₁, R₁ to R₄, L₁, L₂, “a” to “d”, “m”and “n” are the same as defined with respect to Formula 1.

In an embodiment, Formula 1 may be represented by the following Formula6:

In Formula 6, X, A, B, Ar₁, R₁ to R₄, L₁, L₂, “a” to “d”, “m” and “n”are the same as defined with respect to Formula 1.

The monoamine compound represented by Formula 1 according to anembodiment of the present disclosure may be at least one selected fromthe compounds represented in the following Compound Group 1, butembodiments of the present disclosure are not limited thereto:

Referring to FIG. 1 to FIG. 4 again, the organic electroluminescencedevice according to embodiments of the present disclosure will befurther described. The organic layer OL includes the above-describedmonoamine compound according to an embodiment of the present disclosure.For example, the organic layer OL includes the monoamine compoundrepresented by Formula 1.

Hereinafter, explanation will be focused mainly on additional featuresof the monoamine compound according to embodiments of the presentdisclosure and features of the monoamine that are not described will bethe same as the features of the monoamine compound described elsewhereherein.

The first electrode EL1 has conductivity (e.g., electricalconductivity). The first electrode EL1 may be a pixel electrode or ananode. The first electrode EL1 may be a transmissive electrode, atransflective electrode, or a reflective electrode. If the firstelectrode EL1 is the transmissive electrode, the first electrode EL1 mayinclude a transparent metal oxide such as indium tin oxide (ITO), indiumzinc oxide (IZO), zinc oxide (ZnO), and indium tin zinc oxide (ITZO). Ifthe first electrode EL1 is the transflective electrode or the reflectiveelectrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd,Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/AI, Mo, Ti, a compound thereof,or a mixture thereof (for example, a mixture of Ag and Mg). In someembodiments, the first electrode EL1 may have a multilayer structureincluding a reflective layer or a transflective layer, and atransmissive layer formed using ITO, IZO, ZnO, ITZO, etc. For example,the first electrode EL1 may include a three-layer structure ofITO/Ag/ITO.

The thickness of the first electrode EL1 may be from about 1,000 Å toabout 10,000 Å, for example, from about 1,000 Å to about 3,000 Å.

The organic layer OL may be on the first electrode EL1. The organiclayer OL may include a hole transport region HTR, an emission layer EMLand an electron transport region ETR. If the organic layer OL includesthe hole transport region HTR, the emission layer EML and the electrontransport region ETR, at least one of these layers may include themonoamine compound according to an embodiment.

The hole transport region HTR is on the first electrode EL1. The holetransport region HTR may include at least one of a hole injection layerHIL, a hole transport layer HTL, a hole buffer layer, or an electronblocking layer EBL.

The hole transport region HTR may have a single layer formed using asingle material, a single layer formed using a plurality of differentmaterials, or a multilayer structure including a plurality of layersformed using a plurality of different materials.

For example, the hole transport region HTR may have the structure of asingle layer such as a hole injection layer HIL, or a hole transportlayer HTL, and may have a structure of a single layer formed using ahole injection material and a hole transport material. In someembodiments, the hole transport region HTR may have a structure of asingle layer formed using a plurality of different materials, or astructure laminated from the first electrode EL1 of hole injection layerHIL/hole transport layer HTL, hole injection layer HIL/hole transportlayer HTL/hole buffer layer, hole injection layer HIL/hole buffer layer,hole transport layer HTL/hole buffer layer, or hole injection layerHIL/hole transport layer HTL/electron blocking layer EBL, withoutlimitation.

In an embodiment, the hole transport region HTR may include themonoamine compound according to an embodiment of the present disclosure.The hole transport region HTR may have a multilayer structure having aplurality of layers, and one of the plurality of the layers may includethe monoamine compound represented by Formula 1. For example, the holetransport region HTR may include a hole injection layer HIL on the firstelectrode EL1 and the hole transport layer HTL on the hole injectionlayer HIL, and the hole transport layer HTL may include the monoaminecompound represented by Formula 1. However, embodiments of the presentdisclosure are not limited thereto, and for example, the hole injectionlayer HIL may include the monoamine compound of an embodiment.

The hole transport region HTR may include one or two or more kinds ofthe monoamine compound of an embodiment. For example, the hole transportregion HTR may include at least one selected from the compoundsrepresented in Compound Group 1.

The hole transport region HTR may be formed using various suitablemethods such as a vacuum deposition method, a spin coating method, acast method, a Langmuir-Blodgett (LB) method, an inkjet printing method,a laser printing method, and a laser induced thermal imaging (LITI)method.

However, the hole transport region may further include the followingmaterials in each layer.

The hole injection layer HIL may include, for example, a phthalocyaninecompound such as copper phthalocyanine;N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), 4,4′,4′-tris(3-methylphenylphenylamino)triphenylamine(m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris{N,N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate)(PANI/PSS), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPD),triphenylamine-containing polyetherketone (TPAPEK),4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate,or dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile(HAT-CN).

The hole transport layer HTL may include the monoamine compound of anembodiment as described above. Any suitable materials generally used inthe art for hole transport layers may be included in the hole transportlayer, but embodiments of the present disclosure are not limitedthereto. For example, the hole transport layer HTL may include carbazolederivatives such as N-phenyl carbazole and polyvinyl carbazole, fluorinederivatives,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), triphenylamine derivatives such as4,4′,4′-tris(N-carbazolyl)triphenylamine (TCTA),N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPD),4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC),4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), etc.

The electron blocking layer EBL may include, for example, carbazolederivatives such as N-phenyl carbazole and polyvinyl carbazole, fluorinederivatives,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), triphenylamine derivatives such as4,4′,4′-tris(N-carbazolyl)triphenylamine (TCTA),N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPD),4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC),4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), mCP, etc.

The thickness of the hole transport region HTR may be from about 100 Åto about 10,000 Å, for example, from about 100 Å to about 5,000 Å. Thethickness of the hole injection layer HIL may be, for example, fromabout 30 Å to about 1,000 Å, and the thickness of the hole transportlayer HTL may be from about 30 Å to about 1,000 Å. For example, thethickness of the electron blocking layer EBL may be from about 10 Å toabout 1,000 Å. If the thicknesses of the hole transport region HTR, thehole injection layer HIL, the hole transport layer HTL and the electronblocking layer EBL satisfy the above-described ranges, suitable orsatisfactory hole transport properties may be achieved withoutsubstantial increase of a driving voltage.

The hole transport region HTR may further include a charge generatingmaterial in addition to the above-described materials to increaseconductivity (e.g., electrical conductivity). The charge generatingmaterial may be dispersed uniformly or non-uniformly (e.g., irregularly)in the hole transport region HTR. The charge generating material may be,for example, a p-dopant. The p-dopant may be one of quinone derivatives,metal oxides, or cyano group-containing compounds, without limitation.However, embodiments of the present disclosure are not limited thereto.For example, non-limiting examples of the p-dopant may include quinonederivatives such as tetracyanoquinodimethane (TCNQ) and2,3,5,6-tetrafluoro-tetracyanoquinodimethane (F4-TCNQ), metal oxidessuch as tungsten oxide and molybdenum oxide, without limitation.

The hole transport region HTR may further include at least one of a holebuffer layer, or an electron blocking layer EBL. The hole buffer layermay compensate for an optical resonance distance according to thewavelength of light emitted from an emission layer EML and may increaselight emission efficiency. Materials which may be included in a holetransport region HTR may be used as materials which may be included in ahole buffer layer. The electron blocking layer EBL is a layer playingthe role of blocking the electron injection from the electron transportregion ETR to the hole transport region HTR.

The emission layer EML is on the hole transport region HTR. Thethickness of the emission layer EML may be, for example, from about 100Å to about 1,000 Å, or from about 100 Å to about 600 Å. The emissionlayer EML may have a single layer formed using a single material, asingle layer formed using a plurality of different materials, or amultilayer structure having a plurality of layers formed using aplurality of different materials.

As the materials of the emission layer EML, any suitable light-emittingmaterials available in the art may be used, and one selected fromfluoranthene derivatives, pyrene derivative, arylacetylene derivative,anthracene derivatives, fluorene derivatives, perylene derivatives,chrysene derivatives, etc. may be used, without specific limitation. Insome embodiments, pyrene derivatives, perylene derivatives, oranthracene derivatives may be used. For example, as the host material ofthe emission layer EML, anthracene derivatives represented by Formula 7may be used.

In Formula 7, W₁ to W₄ are each independently a hydrogen atom, adeuterium atom, a halogen atom, a substituted or unsubstituted silylgroup, a substituted or unsubstituted alkyl group of 1 to 20 carbonatoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atomsfor forming a ring, or a substituted or unsubstituted heteroaryl groupof 2 to 30 carbon atoms for forming a ring, or may be combined with anadjacent group to form a ring, where m1 and m2 are each independently aninteger of 0 to 4, and m3 and m4 are each independently an integer of 0to 5.

If m1 is 1, W₁ may not be a hydrogen atom, if m2 is 1, W₂ may not be ahydrogen atom, if m3 is 1, W₃ may not be a hydrogen atom, and if m4 is1, W₄ may not be a hydrogen atom.

If m1 is 2 or more, a plurality of W₁ groups are the same or different.If m2 is 2 or more, a plurality of W₂ groups are the same or different.If m3 is 2 or more, a plurality of W₃ groups are the same or different.If m4 is 2 or more, a plurality of W₄ groups are the same or different.

The compound represented by Formula 7 may include the compoundsrepresented by the following structures, but the compound represented byFormula 7 is not limited thereto:

The emission layer EML may include, for example, a fluorescence materialincluding any one selected from the group consisting of spiro-DPVBi,2,2′,7,7′-tetrakis(biphenyl-4-yl)-9,9′-spirobifluorene(spiro-sexiphenyl)(spiro-6P), distyryl-benzene (DSB), distyryl-arylene (DSA), apolyfluorene (PFO)-based polymer and a poly(p-phenylene vinylene)(PPV)-based polymer.

The emission layer EML may further include a dopant, and the dopant mayuse any suitable material available in the art as a dopant. For example,styryl derivatives (for example,1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB),4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene (DPAVB), andN-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine(N-BDAVBi), perylene and the derivatives thereof (for example,2,5,8,11-tetra-t-butylperylene (TBPe)), pyrene and the derivativesthereof (for example, 1,1-dipyrene, 1,4-dipyrenylbenzene,1,4-bis(N,N-diphenylamino)pyrene, and 1,6-bis(N,N-diphenylamino)pyrene),2,5,8,11-tetra-t-butylperylene (TBP),1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi), etc., may be usedas the dopant.

The emission layer EML may include, for example,tris(8-hydroxyquinolino)aluminum (Alq₃),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), poly(N-vinylcarbazole)(PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN),4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA),1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi),3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene(DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2),hexaphenylcyclotrisiloxane (DPSiO₃), octaphenylcyclotetrasiloxane(DPSiO₄), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), etc.

The electron transport region ETR is on the emission layer EML. Theelectron transport region ETR may include at least one of an holeblocking layer HBL, an electron transport layer ETL, or an electroninjection layer EIL, but embodiments of the present disclosure are notlimited thereto.

The electron transport region ETR may have a single layer formed using asingle material, a single layer formed using a plurality of differentmaterials, or a multilayer structure including a plurality of layersformed using a plurality of different materials.

For example, the electron transport region ETR may have the structure ofa single layer such as an electron injection layer EIL, or an electrontransport layer ETL, and may have a structure of a single layer formedusing an electron injection material and an electron transport material.In addition, the electron transport region ETR may have a single layerstructure having a plurality of different materials, or a structurelaminated from the emission layer EML of electron transport layerETL/electron injection layer EIL, or hole blocking layer HBL/electrontransport layer ETL/electron injection layer EIL, without limitation.The thickness of the electron transport region ETR may be, for example,from about 100 Å to about 1,500 Å.

The electron transport region ETR may be formed using various suitablemethods such as a vacuum deposition method, a spin coating method, acast method, a Langmuir-Blodgett (LB) method, an inkjet printing method,a laser printing method, and/or a laser induced thermal imaging (LITI)method.

If the electron transport region ETR includes an electron transportlayer ETL, the electron transport region ETR may includetris(8-hydroxyquinolinato)aluminum (Alq₃),1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene,2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine,bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO),2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene,1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi),2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen),3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ),4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD),bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum(BAlq), berylliumbis(benzoquinolin-10-olate (Bebq2),9,10-di(naphthalene-2-yl)anthracene (ADN), or a mixture thereof.However, embodiments of the present disclosure are not limited thereto.The thickness of the electron transport layer ETL may be from about 100Å to about 1,000 Å and may be, for example, from about 150 Å to about500 Å. If the thickness of the electron transport layer ETL satisfiesthe above-described range, suitable or satisfactory electron transportproperties may be obtained without substantial increase of a drivingvoltage.

If the electron transport region ETR includes the electron injectionlayer EIL, the electron transport region ETR may include a metal halidesuch as LiF, NaCl, CsF, RbCl, RbI, a metal of the lanthanides such as,for example, Yb, a metal oxide such as Li₂O, BaO, or a lithium quinolate(LiQ). However, embodiments of the present disclosure are not limitedthereto. The electron injection layer EIL also may be formed using amixture material of an electron transport material and an insulatingorgano metal salt. The organo metal salt may be a material having anenergy band gap of about 4 eV or more. In some embodiments, the organometal salt may include, for example, metal acetates, metal benzoates,metal acetoacetates, metal acetylacetonates, or metal stearates. Thethickness of the electron injection layer EIL may be from about 1 Å toabout 100 Å, and from about 3 Å to about 90 Å. If the thickness of theelectron injection layer EIL satisfies the above described range,suitable or satisfactory electron injection properties may be obtainedwithout inducing substantial increase of a driving voltage.

The electron transport region ETR may include a hole blocking layer HBLas described above. The hole blocking layer HBL may include, forexample, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(BCP), or 4,7-diphenyl-1,10-phenanthroline (Bphen). However, embodimentsof the present disclosure are not limited thereto.

The second electrode EL2 is provided on the electron transport regionETR. The second electrode EL2 may be a common electrode or a cathode.The second electrode EL2 may be a transmissive electrode, atransflective electrode or a reflective electrode. If the secondelectrode EL2 is the transmissive electrode, the second electrode EL2may include a transparent metal oxide, for example, ITO, IZO, ZnO, ITZO,etc.

If the second electrode EL2 is the transflective electrode or thereflective electrode, the second electrode EL2 may include Ag, Mg, Cu,Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/AI, Mo, Ti, acompound thereof, or a mixture thereof (for example, a mixture of Ag andMg). In some embodiments, the second electrode EL2 may have amultilayered structure including a reflective layer or a transflectivelayer formed using the above-described materials, and a transparentconductive layer formed using ITO, IZO, ZnO, ITZO, etc.

In some embodiments, the second electrode EL2 may be connected with anauxiliary electrode. If the second electrode EL2 is connected with theauxiliary electrode, the resistance of the second electrode EL2 may bedecreased.

In the organic electroluminescence device 10, according to theapplication of a voltage to each of the first electrode EL1 and secondelectrode EL2, holes injected from the first electrode EL1 may move viathe hole transport region HTR to the emission layer EML, and electronsinjected from the second electrode EL2 may move via the electrontransport region ETR to the emission layer EML. The electrons and theholes are recombined in the emission layer EML to produce excitons, andthe excitons may transition (e.g., relax) from an excited state to aground state resulting in the emission of light.

If the organic electroluminescence device 10 is a top emission type (atop emission organic electroluminescence device), the first electrodeEL1 may be a reflective electrode and the second electrode EL2 may be atransmissive electrode or a transflective electrode. If the organicelectroluminescence device 10 is a bottom emission type (a bottomemission organic electroluminescence device), the first electrode EL1may be a transmissive electrode or a transflective electrode and thesecond electrode EL2 may be a reflective electrode.

The organic electroluminescence device 10 according to embodiments ofthe present disclosure includes the monoamine compound of an embodiment,and accordingly, the increase of efficiency and life may be achieved. Inaddition, the effect of decreasing a driving voltage may be achieved.

Hereinafter, embodiments of the present disclosure will be explained inmore detail with reference to examples and comparative examples. Theembodiments are only illustrations for assisting the understanding ofthe present disclosure, and the scope of the present disclosure is notlimited thereto.

Synthetic Examples

The monoamine compound according to an embodiment of the presentdisclosure may be synthesized, for example, as follows. However, thesynthetic method of the monoamine compound according to an embodiment ofthe present disclosure is not limited thereto.

1. Synthesis of Compound 5 (1) Synthesis of Compound A

A-1 (1.1 g), 2,3-dibromo-2,3-dihydrobenzofuran (2.5 g), Pd(PPh₃)₄ (0.5g) and K₂CO₃ (3.1 g) were dissolved in THF (50 ml) and stirred at about80° C. for about 10 hours. The temperature of the reaction solution wasdecreased to room temperature and the reaction was quenched using water.The resultant product was extracted with ethyl ether three times. Theorganic layer thus separated was dried with anhydrous magnesium sulfateand then distilled at a reduced pressure. The crude product thusobtained was separated by column chromatography to obtain IntermediateA-2 (2.6 g, yield: 65%).

Intermediate A-2 (2.6 g) and K₂CO₃ (3.7 g) were dissolved in THF (50 ml)and stirred at about 80° C. for about 3 hours. The temperature of thereaction solution was decreased to room temperature and the reaction wasquenched using water. The resultant product was extracted with ethylether three times. The organic layer thus separated was dried withanhydrous magnesium sulfate and then distilled at a reduced pressure.The crude product thus obtained was separated by column chromatographyto obtain Intermediate A-3 (1.5 g, yield: 80%).

To Intermediate A-3 (1.5 g), Br₂ (1.24 g) dissolved in dichloromethane(30 ml) was added and then, stirred at room temperature for about 3hours. The reaction solution was quenched with water, and an aqueousNa₂S₂O₃ solution (100 ml) was added thereto. Then, the resultant productwas extracted with dichloromethane and water three times. The organiclayer thus separated was dried with anhydrous magnesium sulfate and thendistilled in a reduced pressure. The crude product thus obtained wasseparated by column chromatography to obtain Compound A (1.43 g, yield:70%).

(2) Synthesis of Compound 5

Reactant 5-1 (1.6 g), 3-iodo-9-phenyl-9H-carbazol (4.6 g), Pd₂(dba)₃(0.5 g), PtBu₃ (0.2 ml) and KOtBu (2.8 g) were dissolved in toluene (50ml) and stirred at about 85° C. for about 1 hour. The temperature of thereaction solution was decreased to room temperature and the reaction wasquenched using water. The resultant product was extracted with ethylether three times. The organic layer thus separated was dried withanhydrous magnesium sulfate and then distilled in a reduced pressure.The crude product thus obtained was separated by column chromatographyto obtain Intermediate 5-2 (2.6 g, yield: 65%).

Compound 5 (2.6 g, yield: 80%) was obtained according to substantiallythe same method as in the synthetic method of Intermediate 5-2 exceptfor using Intermediate 5-2 (2.6 g) and Compound A (2.2 g) instead ofreactant 5-1 and 3-iodo-9-phenyl-9H-carbazole.

2. Synthesis of Compound 24

Reactant 24-1 (1.1 g), 2-(4-bromophenyl)dibenzo[b,d]thiophene (3.3 g),Pd₂(dba)₃ (0.5 g), PtBu₃ (0.2 ml) and KOtBu (2.8 g) were dissolved intoluene (50 ml) and stirred at about 85° C. for about 1 hour. Thetemperature of the reaction solution was decreased to room temperatureand the reaction was quenched using water. The resultant product wasextracted with ethyl ether three times. The organic layer thus separatedwas dried with anhydrous magnesium sulfate and then distilled in areduced pressure. The crude product thus obtained was separated bycolumn chromatography to obtain Intermediate 24-2 (2.5 g, yield: 75%).

Compound 24 (2.2 g, yield: 70%) was obtained according to substantiallythe same method as in the synthetic method of Intermediate 24-2 exceptfor using Intermediate 24-2 (2.5 g) and Compound A (2.2 g) instead ofreactant 24-1 and 2-(4-bromophenyl)dibenzo[b,d]thiophene.

3. Synthesis of Compound 32 (1) Synthesis of Reactant C

Intermediate B-1 (2.4 g) was obtained according to substantially thesame method as in the synthetic method of Intermediate A-2 except forusing 2,3-dibromo-2,3-dihydrobenzo[b]thiophene (2.6 g) instead of2,3-dibromo-2,3-dihydrobenzofuran. Intermediate B-2 (1.6 g, yield: 80%)was obtained according to substantially the same method as in thesynthetic method of Intermediate A-3, except that Intermediate B-1 (2.4g) was used instead of Intermediate A-2.

Compound C (1.5 g, yield 70%) was obtained according to substantiallythe same method as in the synthetic method of Compound A, except thatIntermediate B-2 (1.6 g) was used instead of Intermediate A-3.

(2) Synthesis of Compound 32

5-1 (2.0 g), 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.3 g), Pd₂(dba)₃(0.5 g), PtBu₃ (0.2 ml) and KOtBu (2.8 g) were dissolved in toluene (50ml) and stirred at about 85° C. for about 1 hour. The temperature of thereaction solution was decreased to room temperature and the reaction wasquenched using water. The resultant product was extracted with ethylether three times. The organic layer thus separated was dried withanhydrous magnesium sulfate and then distilled in a reduced pressure.The crude product thus obtained was separated by column chromatographyto obtain Intermediate 32-1 (3.5 g, yield: 80%).

Compound 32 (2.5 g, yield: 70%) was obtained according to substantiallythe same method as in the synthetic method of Intermediate 32-1 exceptfor using Intermediate 32-1 (3.5 g) and Compound C (2.3 g) instead ofreactant 5-1 (2.0 g) and 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.3g).

4. Synthesis of Compound 59 (1) Synthesis of Compound D

To D-1 (1.7 g), Br₂ (1.24 g) dissolved in dichloromethane (30 ml) wasadded and stirred at room temperature for about 3 hours. The reactionsolution was quenched with water, and an aqueous Na₂S₂O₃ solution (100ml) was added thereto. Then, the resultant product was extracted withdichloromethane and water three times. The organic layer thus separatedwas dried with anhydrous magnesium sulfate and then distilled in areduced pressure. The crude product thus obtained was separated byrecrystallization to obtain Compound D (1.6 g, yield: 70%).

(2) Synthesis of Compound 59

Reactant 24-1 (1.2 g), 3-iodo-9-phenyl-9H-carbazole (3.4 g), Pd₂(dba)₃(0.5 g), PtBu₃ (0.2 ml) and KOtBu (2.8 g) were dissolved in toluene (50ml) and stirred at about 85° C. for about 1 hour. The temperature of thereaction solution was decreased to room temperature and the reaction wasquenched using water. The resultant product was extracted with ethylether three times. The organic layer thus separated was dried withanhydrous magnesium sulfate and then distilled in a reduced pressure.The crude product thus obtained was separated by column chromatographyto obtain Intermediate 59-1 (2.2 g, yield: 65%).

Compound 59 (2.4 g, yield: 75%) was obtained according to substantiallythe same method as in the synthetic method of Intermediate 59-1 exceptfor using Intermediate 59-1 (2.2 g) and Compound D (2.2 g) instead ofreactant 24-1 and 3-iodo-9-phenyl-9H-carbazole.

5. Synthesis of Compound 67

Intermediate 24-1 (1.2 g), 2-(4-bromophenyl)dibenzo[b,d]furan (3.0 g),Pd₂(dba)₃ (0.5 g), PtBu₃ (0.2 ml) and KOtBu (2.5 g) were dissolved intoluene (50 ml) and stirred at about 85° C. for about 1 hour. Thetemperature of the reaction solution was decreased to room temperatureand the reaction was quenched using water. The resultant product wasextracted with ethyl ether three times. The organic layer thus separatedwas dried with anhydrous magnesium sulfate and then distilled in areduced pressure. The crude product thus obtained was separated bycolumn chromatography to obtain Intermediate 67-1 (2.1 g, yield: 66%).

Compound 67 (3.6 g, yield: 80%) was obtained according to substantiallythe same method as in the synthetic method of Intermediate 67-1 exceptfor using Intermediate 67-1 (2.1 g) and Compound D (2.3 g) instead ofintermediate 24-1 and 2-(4-bromophenyl)dibenzo[b,d]furan.

6. Synthesis of Compound 75 (1) Synthesis of Compound B

Intermediate B-1 (2.4 g) was obtained according to substantially thesame method as in the synthetic method of Intermediate A-2 except forusing 2,3-dibromo-2,3-dihydrobenzo[b]thiophene (2.6 g) instead of2,3-dibromo-2,3-dihydrobenzofuran.

Intermediate B-2 (1.6 g, yield: 80%) was obtained according tosubstantially the same method as in the synthetic method of IntermediateA-3, except that Intermediate B-1 (2.4 g) was used instead ofIntermediate A-2.

Compound B (1.5 g, yield 70%) was obtained according to substantiallythe same method as in the synthetic method of Compound A, except thatIntermediate B-2 (1.6 g) was used instead of Intermediate A-3.

(2) Synthesis of Compound 75

Intermediate 75-1 (1.8 g), 3-iodo-9-phenyl-9H-carbazole (3.9 g),Pd₂(dba)₃ (0.5 g), PtBu₃ (0.2 ml) and KOtBu (2.7 g) were dissolved intoluene (50 ml) and stirred at about 85° C. for about 1 hour. Thetemperature of the reaction solution was decreased to room temperatureand the reaction was quenched using water. The resultant product wasextracted with ethyl ether three times. The organic layer thus separatedwas dried with anhydrous magnesium sulfate and then distilled in areduced pressure. The crude product thus obtained was separated bycolumn chromatography to obtain Intermediate 75-2 (2.0 g, yield: 60%).

Compound 75 (2.5 g, yield: 79%) was obtained according to substantiallythe same method as in the synthetic method of Intermediate 75-2, exceptthat Intermediate 75-2 (2.0 g) and Compound B (2.2 g) were used insteadof Intermediate 75-1 and 3-iodo-9-phenyl-9H-carbazole.

Device Manufacturing Examples

Organic electroluminescence devices of Examples 1 to 6 were manufacturedusing the above-described Compounds 5, 24, 32, 59, 67 and 75,respectively, as materials for a hole transport region.

Example Compounds

Organic electroluminescence devices of Comparative Examples 1 to 4 weremanufactured using Compounds R-1 to R-4, respectively, below asmaterials for a hole transport region.

Comparative Compounds

The organic electroluminescence devices of the Examples and theComparative Examples were manufactured as follows. As an anode, an ITOglass substrate of about 15 Ω/cm² (about 1,200 Å) of Corning Co. was cutto a size of 50 mm×50 mm×0.7 mm and cleansed by ultrasonic waves usingisopropyl alcohol and pure water for 5 minutes, respectively, and thencleansed by irradiating ultraviolet rays for about 30 minutes andexposing to ozone. The glass substrate was installed in a vacuumdeposition apparatus. On the substrate, 2-TNATA was deposited in vacuumas a hole injection material to a thickness of about 600 Å, and theExample Compound or Comparative Compound was deposited in vacuum as ahole transport compound to a thickness of about 300 Å to form a holetransport layer.

On the hole transport layer, 9,10-di(naphthalen-2-yl)anthracene(hereinafter, DNA) as a blue fluorescence host and4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (hereinafter,DPAVBi) as a blue fluorescence dopant were deposited to a weight ratioof 98:2 to a thickness of about 300 Å to form an emission layer.

Then, on the emission layer, Alq₃ was deposited to a thickness of about300 Å as an electron transport layer. On the electron transport layer,alkali metal halide, LiF was deposited to a thickness of about 10 Å asan electron injection layer, and Al was deposited in vacuum to athickness of about 3,000 Å (anode electrode) to form a LiF/AI electrode.An organic electroluminescence device was manufactured. Each layer wasformed by a vacuum deposition method.

Compounds for Forming Device

The respective emission efficiencies of the organic electroluminescencedevices according to Examples 1 to 6 and Comparative Examples 1 to 4 arelisted in Table 1 below. The emission efficiency is a value measured atabout 50 mA/cm², and half life is the test result at 1.0 mA/cm².

TABLE 1 Hole transport Voltage Luminance Efficiency Life layer (V)(cd/m²) (cd/A) (h) Example 1 Example 4.89 3410 6.82 412 Compound 5 Example 2 Example 4.87 3435 6.87 406 Compound 24 Example 3 Example 4.643385 6.77 419 Compound 32 Example 4 Example 4.56 3460 6.92 423 Compound59 Example 5 Example 4.67 3475 6.95 410 Compound 67 Example 6 Example4.87 3300 6.60 405 Compound 75 Comparative Comparative 5.9 2645 5.29 258Example 1 Compound R-1 Comparative Comparative 5.7 3121 5.4 298 Example2 Compound R-2 Comparative Comparative 6.8 2854 5.2 235 Example 3Compound R-3 Comparative Comparative 7.0 2587 5.5 260 Example 4 CompoundR-4

Referring to Table 1, Examples 1 to 6 were found to accomplish a lowvoltage, long life, and high efficiency when compared with ComparativeExamples 1 to 4. Particularly, due to the improving effect of the lifeof the devices of the Example, the life was largely increased whencompared with the Comparative Examples.

While the present disclosure is not limited by any particular mechanismor theory, the monoamine compound according to embodiments of thepresent disclosure is thought to have a highest occupied molecularorbital (HOMO) that is shallower (e.g., that has a lower energy level)than that of the comparative materials, and thus, the device efficiencyand life of the device are thought to be improved, because the chargebalance of holes and electrons is improved through the control of acharge injection rate.

The monoamine compound according to an embodiment of the presentdisclosure is used in a hole transport region and contributes to thedecrease of a driving voltage and the increase of the efficiency andlife of an organic electroluminescence device.

The organic electroluminescence device according to an embodiment of thepresent disclosure has excellent efficiency.

The monoamine compound according to an embodiment of the presentdisclosure may be used as a material for a hole transport region of anorganic electroluminescence device, and by using the monoamine compound,the improving of the efficiency of the organic electroluminescencedevice may be achieved.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting of the presentdisclosure. As used herein, the singular forms “a” and “an” are intendedto include the plural forms as well, unless the context clearlyindicates otherwise. As used herein, the term “and/or” includes any andall combinations of one or more of the associated listed items.

Expressions such as “at least one of,” when preceding a list ofelements, modify the entire list of elements and do not modify theindividual elements of the list.

As used herein, the terms “substantially,” “about,” and similar termsare used as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art. Further, the use of “may” when describing embodiments of thepresent disclosure refers to “one or more embodiments of the presentdisclosure.” As used herein, the terms “use,” “using,” and “used” may beconsidered synonymous with the terms “utilize,” “utilizing,” and“utilized,” respectively. Also, the term “exemplary” is intended torefer to an example or illustration.

Also, any numerical range recited herein is intended to include allsubranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein, and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

Although exemplary embodiments of the present disclosure have beendescribed, it is understood that the present disclosure should not belimited to these exemplary embodiments but various changes andmodifications can be made by one ordinary skilled in the art within thespirit and scope of the appended claims, and equivalents thereof.

What is claimed is:
 1. A compound, represented by the following Formula1:

in Formula 1, X is NAr₂, S, or O, A and B are each independently O or S,Ar₁ and Ar₂ are each independently a substituted or unsubstituted arylgroup of 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroaryl group of 2 to 30 carbon atoms for forming aring, R₁ to R₄ are each independently a hydrogen atom, a deuterium atom,a halogen atom, a cyano group, a substituted or unsubstituted alkylgroup of 1 to 20 carbon atoms, a substituted or unsubstituted aryl groupof 6 to 30 carbon atoms for forming a ring, or a substituted orunsubstituted heteroaryl group of 2 to 30 carbon atoms for forming aring, L₁ and L₂ are each independently direct linkages, substituted orunsubstituted arylene groups of 6 to 30 carbon atoms for forming a ring,or substituted or unsubstituted heteroarylene groups of 2 to 30 carbonatoms for forming a ring, except when both L₁ and L₂ are directlinkages, “a” and “b” are each independently integers of 0 to 4, “c” and“d” are each independently integers of 0 to 3, and “m” and “n” are eachindependently integers of 0 to
 2. 2. The compound of claim 1, whereinFormula 1 is represented by the following Formula 2 or Formula 3:

in Formula 2 and Formula 3, X, Ar₁, R₁ to R₄, L₁, L₂, “a” to “d”, “m”and “n” are the same as defined with respect to Formula
 1. 3. Thecompound of claim 1, wherein Formula 1 is represented by the followingFormula 4 or Formula 5:

in Formula 4 and Formula 5, X, Ar₁, R₁ to R₄, L₁, L₂, “a” to “d”, “m”and “n” are the same as defined with respect to Formula
 1. 4. Thecompound of claim 1, wherein: “m” and “n” are each independently 0 or 1,and L₁ and L₂ are each independently a direct linkage or a substitutedor unsubstituted arylene group of 6 to 12 carbon atoms for forming aring.
 5. The compound of claim 1, wherein Ar₁ is a substituted orunsubstituted aryl group of 6 to 18 carbon atoms for forming a ring. 6.The compound of claim 1, wherein Formula 1 is represented by thefollowing Formula 6:

in Formula 6, X, A, B, Ar₁, R₁ to R₄, L₁, L₂, “a” to “d”, “m” and “n”are the same as defined with respect to Formula
 1. 7. The compound ofclaim 1, wherein R₁ to R₄ are each independently a hydrogen atom, adeuterium atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group of 1 to 20 carbon atoms, or an unsubstitutedaryl group of 6 to 30 carbon atoms for forming a ring.
 8. The compoundof claim 1, wherein the compound represented by Formula 1 is at leastone selected from compounds represented in the following Compound Group1: